DE2322673A1 - Neue verbindungen vom prostaglandintyp und verfahren zu ihrer herstellung - Google Patents
Neue verbindungen vom prostaglandintyp und verfahren zu ihrer herstellungInfo
- Publication number
- DE2322673A1 DE2322673A1 DE2322673A DE2322673A DE2322673A1 DE 2322673 A1 DE2322673 A1 DE 2322673A1 DE 2322673 A DE2322673 A DE 2322673A DE 2322673 A DE2322673 A DE 2322673A DE 2322673 A1 DE2322673 A1 DE 2322673A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compounds
- optically active
- methyl
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
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- 238000000034 method Methods 0.000 title claims description 61
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- 150000003180 prostaglandins Chemical class 0.000 title description 28
- 238000004519 manufacturing process Methods 0.000 title description 9
- -1 phosphonate anion Chemical class 0.000 claims description 121
- 125000004432 carbon atom Chemical group C* 0.000 claims description 65
- 239000001257 hydrogen Substances 0.000 claims description 64
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- 239000002253 acid Chemical group 0.000 claims description 59
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 44
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- 238000006243 chemical reaction Methods 0.000 claims description 31
- 238000002360 preparation method Methods 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 230000009467 reduction Effects 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
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- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 12
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- 238000006297 dehydration reaction Methods 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- SXXLKZCNJHJYFL-UHFFFAOYSA-N 4,5,6,7-tetrahydro-[1,2]oxazolo[4,5-c]pyridin-5-ium-3-olate Chemical compound C1CNCC2=C1ONC2=O SXXLKZCNJHJYFL-UHFFFAOYSA-N 0.000 claims description 6
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- BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 claims 1
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- 238000005481 NMR spectroscopy Methods 0.000 description 15
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- 229940001593 sodium carbonate Drugs 0.000 description 1
- 229940076133 sodium carbonate monohydrate Drugs 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- UNFWWIHTNXNPBV-WXKVUWSESA-N spectinomycin Chemical compound O([C@@H]1[C@@H](NC)[C@@H](O)[C@H]([C@@H]([C@H]1O1)O)NC)[C@]2(O)[C@H]1O[C@H](C)CC2=O UNFWWIHTNXNPBV-WXKVUWSESA-N 0.000 description 1
- 229960000268 spectinomycin Drugs 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 229960004306 sulfadiazine Drugs 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000011477 surgical intervention Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000001975 sympathomimetic effect Effects 0.000 description 1
- 229940064707 sympathomimetics Drugs 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 230000035884 vasodepression Effects 0.000 description 1
- 229960003726 vasopressin Drugs 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/252,030 US4304907A (en) | 1972-05-10 | 1972-05-10 | Bicyclo lactone intermediates for prostaglandin analogs |
US05/426,058 US4303796A (en) | 1972-05-10 | 1973-12-19 | 16-Phenoxy prostaglandin F2α analogs |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2322673A1 true DE2322673A1 (de) | 1973-11-22 |
Family
ID=26941978
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2322673A Withdrawn DE2322673A1 (de) | 1972-05-10 | 1973-05-05 | Neue verbindungen vom prostaglandintyp und verfahren zu ihrer herstellung |
Country Status (8)
Country | Link |
---|---|
US (8) | US4304907A (xx) |
AU (1) | AU470415B2 (xx) |
BE (1) | BE799372A (xx) |
CH (2) | CH585711A5 (xx) |
DE (1) | DE2322673A1 (xx) |
FR (1) | FR2184007B1 (xx) |
GB (3) | GB1409842A (xx) |
NL (1) | NL7306462A (xx) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2601646A1 (de) * | 1975-01-24 | 1976-07-29 | Lepetit Spa | Neue prostaglandin-analoga |
Families Citing this family (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3864387A (en) * | 1973-05-21 | 1975-02-04 | Upjohn Co | 5-Oxa phenyl-and phenoxy-substituted prostaglandin F{HD 1{301 {0 {B analogs |
GB1502610A (en) * | 1974-12-12 | 1978-03-01 | Ici Ltd | Process for the preparation of prostaglandin intermediate |
US4032561A (en) * | 1975-05-27 | 1977-06-28 | The Upjohn Company | 17-Phenyl-18,19,20-trinor-cis-4,5-didehydro-PGF1.sub.α compounds |
DE2655004C3 (de) * | 1976-12-02 | 1980-06-19 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Verfahren zur Herstellung von bicyclischen Laktonen |
US4149006A (en) * | 1977-01-24 | 1979-04-10 | G. D. Searle & Co. | Prostaglandin derivatives having alkynyl, hydroxy and aryloxy junctions in the 2β side chain |
DE3268099D1 (en) * | 1982-06-15 | 1986-02-06 | Ibm | Method and apparatus for controlling access to a communication network |
US4912235A (en) * | 1983-12-22 | 1990-03-27 | Syntex (U.S.A.) Inc. | Processes and intermediates for making 16-phenoxy- and 16-substituted phenoxy-prostatrienoic acid derivatives and their stereoisomers |
US4804787A (en) * | 1983-12-22 | 1989-02-14 | Syntex (U.S.A.) Inc. | Processes and intermediates for making 16-phenoxy and 16-substituted phenoxy-prostatrienoic acid derivatives |
US4600785A (en) * | 1983-12-22 | 1986-07-15 | Syntex (U.S.A.) Inc. | Processes and intermediates for making 16-phenoxy and 16-substituted phenoxy-prostatrienoic acid derivatives |
US4929740A (en) * | 1984-10-09 | 1990-05-29 | Syntex (U.S.A.) Inc. | Process for making 16-phenoxy- and 16-(substituted phenoxy)-prostatrienoic acid derivatives |
US4778904A (en) * | 1985-09-13 | 1988-10-18 | Syntex (U.S.A.) Inc. | Intermediates for making 16-phenoxy- and 16-(substituted phenoxy)-prostatrienoic acid derivatives |
US4755531A (en) * | 1986-08-11 | 1988-07-05 | Syntex (U.S.A.) Inc. | Thiol esters of 4,5-allenyl prostaglandins and use thereof as antigastric secretion agents |
CS264861B1 (en) * | 1986-12-12 | 1989-09-12 | Kral Josef | Agent for cow natality increase |
US6187813B1 (en) | 1990-04-10 | 2001-02-13 | Pharmacia & Upjohn Aktiebolag | Prostaglandin derivatives for the treatment of glaucoma or ocular hypertension |
US5296504A (en) * | 1988-09-06 | 1994-03-22 | Kabi Pharmacia | Prostaglandin derivatives for the treatment of glaucoma or ocular hypertension |
ES2213504T1 (es) * | 1988-09-06 | 2004-09-01 | Pfizer Health Ab | Derivados de prostaglandina para el tratamiento del glaucoma o hipertension ocular. |
US5321128A (en) * | 1988-09-06 | 1994-06-14 | Kabi Pharmacia Ab | Prostaglandin derivatives for the treatment of glaucoma or ocular hypertension |
JP3097145B2 (ja) * | 1991-02-27 | 2000-10-10 | 日産化学工業株式会社 | コーリーラクトンジオールの光学分割方法 |
EP0638605B1 (en) * | 1993-08-10 | 1998-12-09 | Shin-Etsu Chemical Co., Ltd. | Process for preparing a polyester-modified silicone resin and a curable composition comprising the polyester-modified silicone resin |
US20020037914A1 (en) | 2000-03-31 | 2002-03-28 | Delong Mitchell Anthony | Compositions and methods for treating hair loss using C16-C20 aromatic tetrahydro prostaglandins |
US20020013294A1 (en) | 2000-03-31 | 2002-01-31 | Delong Mitchell Anthony | Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives |
US20020172693A1 (en) | 2000-03-31 | 2002-11-21 | Delong Michell Anthony | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
WO2010102078A1 (en) | 2009-03-04 | 2010-09-10 | Allergan, Inc. | Enhanced bimatoprost ophthalmic solution |
US7851504B2 (en) | 2005-03-16 | 2010-12-14 | Allergan, Inc. | Enhanced bimatoprost ophthalmic solution |
US8623918B2 (en) | 2008-10-29 | 2014-01-07 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
US8722739B2 (en) | 2008-10-29 | 2014-05-13 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
US20110293549A1 (en) | 2009-02-03 | 2011-12-01 | Athena Cosmetics, Inc. | Composition, method and kit for enhancing hair |
WO2010108012A1 (en) * | 2009-03-18 | 2010-09-23 | Duke University | Compositions and methods for promoting nasal patency and treating neurogenic bladder using prostaglandins |
US9522153B2 (en) | 2009-12-22 | 2016-12-20 | Allergan, Inc. | Compositions and methods for lowering intraocular pressure |
US20110206647A1 (en) * | 2010-02-25 | 2011-08-25 | Abt Holding Company | Modulation of Angiogenesis |
SG10201913904PA (en) * | 2010-02-25 | 2020-03-30 | Abt Holding Co | Modulation of angiogenesis |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3505386A (en) * | 1965-12-29 | 1970-04-07 | Upjohn Co | Compounds related to prostaglandins |
US3711528A (en) * | 1970-04-06 | 1973-01-16 | Upjohn Co | Racemic dihydro-pge{11 {11 and related compounds |
US3711515A (en) * | 1970-11-27 | 1973-01-16 | Upjohn Co | Tricyclic lactone alkene or alkenyne |
IE37602B1 (en) * | 1971-05-11 | 1977-08-31 | Ici Ltd | Cyclopentane derivatives |
US4024179A (en) * | 1972-11-08 | 1977-05-17 | Pfizer Inc. | Substituted ω-pentanorprostaglandins |
-
1972
- 1972-05-10 US US05/252,030 patent/US4304907A/en not_active Expired - Lifetime
-
1973
- 1973-04-30 AU AU55006/73A patent/AU470415B2/en not_active Expired
- 1973-05-02 GB GB379075A patent/GB1409842A/en not_active Expired
- 1973-05-02 GB GB2091873A patent/GB1409841A/en not_active Expired
- 1973-05-02 GB GB379175A patent/GB1409843A/en not_active Expired
- 1973-05-05 DE DE2322673A patent/DE2322673A1/de not_active Withdrawn
- 1973-05-09 NL NL7306462A patent/NL7306462A/xx not_active Application Discontinuation
- 1973-05-09 FR FR7316720A patent/FR2184007B1/fr not_active Expired
- 1973-05-10 BE BE130979A patent/BE799372A/xx not_active IP Right Cessation
- 1973-05-10 CH CH668973A patent/CH585711A5/xx not_active IP Right Cessation
- 1973-05-10 CH CH584176A patent/CH585712A5/xx not_active IP Right Cessation
- 1973-12-19 US US05/426,058 patent/US4303796A/en not_active Expired - Lifetime
-
1977
- 1977-02-07 US US05/766,011 patent/US4116989A/en not_active Expired - Lifetime
- 1977-02-07 US US05/766,010 patent/US4116988A/en not_active Expired - Lifetime
- 1977-02-07 US US05/765,919 patent/US4096335A/en not_active Expired - Lifetime
- 1977-02-07 US US05/765,997 patent/US4087616A/en not_active Expired - Lifetime
- 1977-02-10 US US05/767,444 patent/US4096179A/en not_active Expired - Lifetime
- 1977-02-10 US US05/767,443 patent/US4096178A/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2601646A1 (de) * | 1975-01-24 | 1976-07-29 | Lepetit Spa | Neue prostaglandin-analoga |
Also Published As
Publication number | Publication date |
---|---|
BE799372A (fr) | 1973-11-12 |
US4116988A (en) | 1978-09-26 |
GB1409843A (en) | 1975-10-15 |
AU5500673A (en) | 1974-10-31 |
GB1409841A (en) | 1975-10-15 |
AU470415B2 (en) | 1976-03-18 |
US4087616A (en) | 1978-05-02 |
CH585712A5 (xx) | 1977-03-15 |
US4304907A (en) | 1981-12-08 |
US4303796A (en) | 1981-12-01 |
US4096179A (en) | 1978-06-20 |
NL7306462A (xx) | 1973-11-13 |
CH585711A5 (xx) | 1977-03-15 |
FR2184007B1 (xx) | 1979-01-12 |
US4096335A (en) | 1978-06-20 |
FR2184007A1 (xx) | 1973-12-21 |
US4116989A (en) | 1978-09-26 |
GB1409842A (en) | 1975-10-15 |
US4096178A (en) | 1978-06-20 |
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Legal Events
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OD | Request for examination | ||
8130 | Withdrawal |